ATE49967T1 - PROCESS FOR THE PREPARATION OF N-METHYL DERIVATIVES OF METHYLESTER OF DIHYDROLYSERGINE ACID OR OF METHYLESTER OF METHOXYLUMILYSERGINE ACID. - Google Patents
PROCESS FOR THE PREPARATION OF N-METHYL DERIVATIVES OF METHYLESTER OF DIHYDROLYSERGINE ACID OR OF METHYLESTER OF METHOXYLUMILYSERGINE ACID.Info
- Publication number
- ATE49967T1 ATE49967T1 AT86401540T AT86401540T ATE49967T1 AT E49967 T1 ATE49967 T1 AT E49967T1 AT 86401540 T AT86401540 T AT 86401540T AT 86401540 T AT86401540 T AT 86401540T AT E49967 T1 ATE49967 T1 AT E49967T1
- Authority
- AT
- Austria
- Prior art keywords
- methylester
- acid
- formula
- denotes
- methyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 2
- 150000004702 methyl esters Chemical class 0.000 title 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 abstract 1
- 150000008046 alkali metal hydrides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000012022 methylating agents Substances 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A process for preparing an N-methyl derivative of methyl dihydrolysergate and methyl methoxylumilysergate, of formula: <IMAGE> in which R1 denotes a hydrogen atom or a methoxy group, which comprises reacting a methylating agent with a compound of formula: <IMAGE> in which R1 is defined as above, in the presence of a quaternary salt, in the presence of a solid metal alcoholate of formula CH3-OM in which M denotes an alkali metal atom, or an alkali metal hydride, and in the presence of a dehydrating agent of formula R2-COO-CH3 in which R2 denotes a hydrogen atom or an alkyl, alkyloxy, alkyloxycarbonyl or aryl group or of formula R3-C(OCH3)3 in which R3 denotes a hydrogen atom, an alkyl group or an aryl group.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8510622A FR2584721B1 (en) | 1985-07-11 | 1985-07-11 | PROCESS FOR THE PREPARATION OF N-METHYL DERIVATIVES OF METHYL DIHYDROLYSERGATE OR METHYL METHOXYLUMILYSERGATE |
| EP86401540A EP0211728B1 (en) | 1985-07-11 | 1986-07-10 | Process for the preparation of the n-methyl derivatives of the methyl ester of dihydrolysergic acid or of the methyl ester of methoxylumilysergic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE49967T1 true ATE49967T1 (en) | 1990-02-15 |
Family
ID=9321197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT86401540T ATE49967T1 (en) | 1985-07-11 | 1986-07-10 | PROCESS FOR THE PREPARATION OF N-METHYL DERIVATIVES OF METHYLESTER OF DIHYDROLYSERGINE ACID OR OF METHYLESTER OF METHOXYLUMILYSERGINE ACID. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4739061A (en) |
| EP (1) | EP0211728B1 (en) |
| JP (1) | JPH0667937B2 (en) |
| KR (1) | KR930010499B1 (en) |
| AT (1) | ATE49967T1 (en) |
| CA (1) | CA1246552A (en) |
| DE (1) | DE3668620D1 (en) |
| ES (1) | ES2000332A6 (en) |
| FR (1) | FR2584721B1 (en) |
| GR (1) | GR861784B (en) |
| PT (1) | PT82936B (en) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL294949A (en) * | ||||
| US3228940A (en) * | 1966-01-11 | Methyl- and i,g-dimethyl-ergoline nitriles | ||
| US3228941A (en) * | 1966-01-11 | Methyl and i,g-dimethyl-ergoline i derivatives | ||
| CH344731A (en) * | 1956-05-18 | 1960-02-29 | Sandoz Ag | Process for the production of new derivatives of the lysergic acid series alkylated on the indole nitrogen |
| US3228943A (en) * | 1962-06-11 | 1966-01-11 | Lumilysergol derivatives | |
| DE1936410A1 (en) * | 1969-07-17 | 1971-02-11 | Hoechst Ag | O-acyl lysergols and process for their preparation |
| US3879554A (en) * | 1970-03-20 | 1975-04-22 | Farmaceutici Italia | Use of 1,6-dimethyl-8-{62 -(5-bromonicotinoyloxymethyl)-10 {60 -methoxyergoline in treating cerebral and peripheral metabolic vascular disorders |
| YU40004B (en) * | 1977-07-21 | 1985-06-30 | Lek Tovarna Farmacevtskih | Praocess for preparing n-substituted esters of 9,10-dihydrlysergic acid |
| GB2013194B (en) * | 1978-01-26 | 1982-09-22 | Simes | Carbamates of monolysergols (8 beta hydroxy ethylergolines) |
| IT1094965B (en) * | 1978-04-05 | 1985-08-10 | Corvi Mora E | LISERGOL DERIVATION PREPARATION PROCEDURE |
| JPH0924820A (en) * | 1995-07-13 | 1997-01-28 | Aisin Seiki Co Ltd | Negative pressure booster |
-
1985
- 1985-07-11 FR FR8510622A patent/FR2584721B1/en not_active Expired
-
1986
- 1986-07-07 PT PT82936A patent/PT82936B/en not_active IP Right Cessation
- 1986-07-09 GR GR861784A patent/GR861784B/en unknown
- 1986-07-09 CA CA000513401A patent/CA1246552A/en not_active Expired
- 1986-07-10 AT AT86401540T patent/ATE49967T1/en not_active IP Right Cessation
- 1986-07-10 JP JP61160972A patent/JPH0667937B2/en not_active Expired - Fee Related
- 1986-07-10 US US06/884,036 patent/US4739061A/en not_active Expired - Lifetime
- 1986-07-10 DE DE8686401540T patent/DE3668620D1/en not_active Expired - Fee Related
- 1986-07-10 KR KR1019860005573A patent/KR930010499B1/en not_active Expired - Fee Related
- 1986-07-10 EP EP86401540A patent/EP0211728B1/en not_active Expired - Lifetime
- 1986-07-11 ES ES8600253A patent/ES2000332A6/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0211728B1 (en) | 1990-01-31 |
| US4739061A (en) | 1988-04-19 |
| JPS6219586A (en) | 1987-01-28 |
| FR2584721B1 (en) | 1987-10-02 |
| PT82936B (en) | 1989-01-30 |
| CA1246552A (en) | 1988-12-13 |
| ES2000332A6 (en) | 1988-02-16 |
| KR930010499B1 (en) | 1993-10-25 |
| JPH0667937B2 (en) | 1994-08-31 |
| FR2584721A1 (en) | 1987-01-16 |
| KR870001209A (en) | 1987-03-12 |
| EP0211728A1 (en) | 1987-02-25 |
| DE3668620D1 (en) | 1990-03-08 |
| GR861784B (en) | 1986-11-10 |
| PT82936A (en) | 1986-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |